Dichroic dye for polarization film, composition comprising the same for polarization film, method for forming polarization plate and polarization plate prepared thereby

A dichroic dye comprising a structure of (reactive end functional group)-L1-(M,L,D),

• wherein D is at least one of dichroic structure selected from the group consisting of azo, anthraquinone, azomethine, indigo, thioindigo, cyanine, indane, azulene, perylene, phthaloperin, and azine dyes;
• wherein the azo dye is at least one selected from the group consisting of
• (wherein R1-R16 are substituents which are selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups;
• and coupled with R5 and R6 or R7 and R8 can be coupled to form phenyl groups);
• wherein the anthraquinone dye is at least one selected from the group consisting of
• (wherein R1-R6 are substituents which are selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups,
• (wherein, R7 is defined the same as in R1-R6), and imide groups);
• wherein the azomethine dye is at least one selected from the group consisting of
• (wherein R1-R12are substituents selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups);
• wherein the indigo or the thioindigo dye is at least one selected from the group consisting of
• (wherein R1-R14 are substituents which are selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups);
• wherein the cyanine dye is at least one selected from the group consisting of
• wherein the indane dye is at least one selected from the group consisting of
• (wherein, R1-R2 are substituents selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups);
• wherein the azulene dye is at least one selected from the group consisting of
• (wherein R1-R10 are substituents selected from the group consisting of hydrogen, C1-C20straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups);
• wherein the perylene dye is at least one selected from the group consisting of
• (wherein R1-R8are substituents selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl,1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1- C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups);
• wherein the phthaloperin dye is at least one selected from the group consisting of
• (wherein, R1-R8 are substituents selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups);
• wherein the azine dye is at least one selected from the group consisting of
• (wherein, R1-R12are substituents selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbomyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups);
• wherein M is at least one of a structure with liquid crystal properties selected from the group consisting of
• (where Z represents —COO—, —OCO—, —CH2CH2—, —CH═CH—, —C≡C— or a single bond and R1-R12 are substituents selected from the group consisting of hydrogen, C1-C20 straight or branched chain alkyl groups such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl, pentyl, hexyl, heptyl, heptyl, octyl, 2-ethylhexyl, dodecyl, hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, 1-norbornyl, and 1-adamantyl, halogen groups such as fluorine, chlorine, bromine, and iodine, C1-C20 alkoxy groups, C1-C20 aliphatic groups, C1-C20 aliphatic amino groups, C1-C20 aliphatic imino groups, C1-C20 aliphatic alkyl imino groups, C6-C20 aryl groups, C5-C20 hetero ring groups, cyano groups, C1-C20 carboxyl groups, carbamoyl groups, C1-C20 aliphatic oxy carbonyl groups, C6-C20 aryl oxy carbonyl groups, C1-C20 acyl groups, hydroxyl groups, C1-C20 aliphatic oxy groups, C6-C20 aryloxy groups, C1-C20 acyloxy groups, carbamoyloxy groups, C5-C20 hetero ring oxy groups, C1-C20 aliphatic oxy carbonyloxy groups, N-C1-C20 alkylacylamino groups, carbamoylamino groups, sulfamoylamino groups, C1-C20 aliphatic oxy carbonylamino groups, C6-C20 aryloxycarbonylamino groups, C1-C20 aliphatic sulfonylamino groups, C5-C20 arylsulfonylamino groups, C1-C20 aliphatic thio groups, C6-C20 arylthio groups, C1-C20 aliphatic sulfonyl groups, C6-C20 arylsulfonyl groups, sulfamoyl groups, sulfo groups, and imide groups);
• wherein L and L1 are linking structures which are the same or different from each other and are selected from the group consisting of
• (wherein, n represents integer from 1 to 12);
• wherein the reactive end functional group is selected from the group consisting of
• wherein the structure of (M,L,D) includes one structure M with liquid crystal properties and one to three dichroic structures (D1, D2, and D3);
• if the structure of (M,L,D) includes two or more dichroic structures, the dichroic structures are coupled directly to each other or through a linking structure (L);
• the structure M is coupled to the dichroic structures (D1, D2, or D3) by the linking structure (L), and the dichroic structures (D1, D2, and D3) are different from each other.